Hydrochloric Acid → 3-(1-Methylethyl)-2,4-imidazolidinedione

HRID 1058940Notes

Reaction equation

HRID 1058940 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][C:5]([OH:7])=O.[CH:8]([N:11]=[C:12]=[O:13])([CH3:10])[CH3:9].Cl>O>[CH:8]([N:11]1[C:5](=[O:7])[CH2:4][NH:3][C:12]1=[O:13])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 14798Sodium HydroxideHCID 61277Isopropyl isocyanate

Product 1

HCID 5680853-(1-Methylethyl)-2,4-imidazolidinedione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 3.6 g of sodium hydroxide in 75 ml of water was added 7.5 g of glycine. The solution was cooled to 5° C. and treated with 9.8 ml of isopropylisocyanate. After 5 h the reaction mixture was neutralised with 50 ml concentrated hydrochloric acid added dropwise to the slurry. This mixture was refluxed for 2 h then cooled to rt. The product was extracted with ethyl acetate to give 10.9 g of a colourless oil. 1H NMR (400 MHz, deuteriochloroform): δ=1.45 (6H, d, J=7 Hz), 3.92 (2H, s), 4.35 (1H, septet, J=7 Hz), 6.39 (1H, br s).

Workup

  1. additionadded dropwise to the slurry
  2. temperatureThis mixture was refluxed for 2 h
  3. temperaturethen cooled to rt
  4. extractionThe product was extracted with ethyl acetate

Sources & evidence

ORD record
ord-0aa1bf0a66844039823c660f52cf5b76
Source dataset
uspto-grants-2003_02
Patent number
US06518293B2

Reaction notes

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